Azo-dyestuffs and process of making same



Patented Aug. 16, 1932 UNITED STATES PATENT oFFicE;

GERALD BONHGTE, OE BASE-L, SYVITZERLAND, ASSIGNOR '10 SOCIETY OF CHEMICAL v INDUSTRY IN BASLE, OF BASEL, SWITZERLAND AZO-DYESTUFFS Ann rnocnss or MAKING SAM N0 Drawing. Application filed October 21, 1931, Serial No. 570,263, and in Switzerland October 25, 1930.7

The present invention relates to the manufacture of new azo-dyestuffs. It comprises the process of making these dyestuffs, and the new clyestufis themselves. or 1 It has been found that new dyestuffs are obtained by coupling an arylide of'2: 3-hy- Among these a cidylated paraphenylenediamine derivatives those are particularly valuables which correspond to the general formula" V L droxynaphthoic acid or a derivative thereof further substituted in the naphthalene nucleus and capable of coupling in l position, with the diazo-compound of a monoacidylated paraphenylenediamine of the general a formula wherein .2 stands for a residue containing an of coupling, such-as for example or the like, and further wherein the aryl nucleus of the paraphenylenediamine can carry substituent-s from a group. of substituent-s consisting of halogen, alkyl or alkoxy.

in which one of the ws stands for a substituent of the group consisting of halogen, alkyl or alkoxy, the other w stands for a hydrogen atom or for a substituent of the just defined group, "3 stands for O or S, and in which the unsulfonated .aryl radicle which is incapable aryl nucleus linked to the bridge can also carry substituents of the above defined group.

The new dyestuffs, which therefore correspond to the general formula E xample 1 28.6 parts of l-amino-2zS-dimethoXylhenylacetylaminohenzene are diazot zed n the usual manner and introduced into a solution of 26.3. parts of the anilide of 2:3l1y

droxynaphthoic acid, 50 parts of caustic soda esolution of 3G 'p r cent. strength, 3 parts of calcined sodium carbonate and 2 0 parts of water,

The dyestuif which is formed and which corresponds to the formula e-eaQ .O-CH:

precipitate which is separated by filtration and dried.

Example 2 Cotton yarn is impregnated with a solution containing per liter 5 grams of 2: 3-hydroxynaphthoic acid-a-naphthylamide, 10 cc. of caustic soda solution of 3l Be. and 10 cc. of Turkey red oil. The material is well wrung out and the dyeing is developed in a diazosolution which has been neutralized by means of sodium bicarbonate and contains per liter the diazo-compound from 3 grams of 1- amino-2 5-dimethoXy-el-phenylacetyl-aminobenzene; the material is then rinsed and soaped. There is obtained a pure blue dyeing of very good fastness properties.

Similar shades are obtained by using other arylides of 2:3-hydroxynaphthoic acid, for

remarkably fast. 7

example, the ,B-naphthylamide or the orthotoluidide. Violet shades are for example obtained by using the ortho or para-anisidide, the 5-chloro-2-toluidide or the para-chloranilide of 2: 3-hydroxynaphthoic acid.

Similar results are obtained in piece dyeing or in printing.

Example 3 Cotton yarn is impregnated at 25-30 (3., with a solution containing per liter 3 grams of 2: 3'-hydroxynaphthoic acid para-chloranilide, 6 cc. of caustic soda, solution of 34 B., c. ofiTu-rkey red oil and 3 cc. of a solution of formaldehyde of 40 per cent. strength,

"the proportion ofgoods to liquor being 1 :20.

' 'fviolet dyeing of very good properties of fastness." The dyestuii thus produced on the fiber a so c r esponds to he formula Cotton yarn is impregnated with an alkaline grounding liquor containing'p'er liter 4 grams or" 2 8=h-ydroxynaphthoic acid ortholiter the diaz o-compound from 2 grams of 4 1"-meth;yl)- phenOXy acet-ylaminO 2: 5- dimethoxy-1-amino-benzene. There is obtained apu re greenish-blue dyeing which is The following table gives the shades on cotton-producedWith some further dyestuffs What I claim is 1. As new products the unsulfonated azodyestuffs of the general formula wherein 2 stands for a residue containing a radicle of the benzene or of the naphthalene series incapable of coupling, which products are dark red to violet and blue powders, and which, when produced on the fiber, dye the same similar tints.

2. As new products the unsulfonated azodyestuffs of the general formula O H V a: 5H

wherein one of the ms stands for a substituent from a group consisting of halogen,-alkylj or alkoXy, the other 00 stands for a hydrogen atom or a substituent of the above defined tr 0 f H group, and wherein the aryl nucleus attached to the oxygen bridge may also carry substituents of the above defined group, which products are dark red to violet and blue powders, and which, when produced on the fiber, dye the same similar tints.

4; As new products the unsulfonated azodyestuffs of the general formula wherein one of the ws stands for a substituent from a group consisting of halogen, alkyl or alkoxy, and the other m stands for a hydrogen atom or a substituent of the above defined group, which products are dark red to violet and blue powders, and which, when produced on the fiber, dye the same similar tints.

5. As new products the unsulfonated azodyestufis of the general formula wherein the two 50 s stand for alkyl or alkoxy,

;' which products are dark red to violet-and blue powders, and which, when produced on the fiber, dye the same similar tints.

6. As a new product the unsulfonated azodyestuff, of the formula A O-CHa CH3 OCHz-CNON= I 6 a (5-011. on 0- o I V C1Hs which product is a blue-Violet powder, yielding on cotton after soaping fast blue tints.

7. As a new product the unsulfonated azodyestuff of the formula o-om 7 on (jg-1 10 o n NO:

which product is a blue-violet powder, yielding on cotton after soaping fast violet tints. 8. As a new product the unsulfonated azodyestuff of the formula N=N on; orr= if tn O-on;

ii a

which product is a blue-violet powder, yielding on cotton after soaping fast violet tints. In witness whereof I have'hereunto signed my name this 10th day of October, 1931.

GERALD BONHOTE. 

